13 Life-Changing Lessons in Leadership

Time to read: 18:20

Early on in my career, I worked at a small Information Technology consultancy and oversaw many aspects of the business. Because it was my first job out of college, I was understandably unsure of the many decisions I was suddenly making for the firm. During my catch-ups, I would ask my boss, who was the owner and CEO, what I should do at all of the many decision-making points in front of me.

At some point, he stopped this habit and told me to make decisions myself. He said, “If you make the wrong decision, you’ll probably hear my mouth—but, right or wrong, you have to make a decision and run with it.”

This experience taught me a valuable lesson, and there is a moral to this story:

When pitted against decisions, make a call and take action instead of being indecisive and letting valuable time pass by.

We’ve all worked with great leaders who have ideas, mindsets, and beliefs that have helped them succeed in their careers. These leaders have the ability to leave a lasting impression in our minds, and it’s usually a learning that follows us and helps us make good choices throughout our careers.

At Local Wisdom, we work with many executives and their communicators and we understand firsthand how to continuously find new opportunities and actively move the entire company to new heights. This is why I jumped on the opportunity to serve as the chairperson for the Advance Learning Institute’s Leadership & Executive Communications conference in Chicago. I got the chance to spend 3 days meeting with creative communicators and introducing thought-provoking speakers.

I asked all of the speakers to answer one question that would help me make their introductions more meaningful:

What’s one learning experience you gained from a leader you’ve worked with that you are most thankful for?

I thought their stories had very powerful nuggets of wisdom, and it would be a shame not to share them here. 

Elizabeth Clements

Executive Director, Internal and Executive Communications, DePaul University

“I once reported to a director of communications in the science communication world [who] was fearless when it came to implementing new ideas. She once threw a 1000-person pajama party at 2 AM to witness a particle accelerator turn on in Europe. Why not? She also struck fear into my heart every time I had to turn in a writing assignment. She had her grammatical pet peeves, as we all do, but hers will forever be ingrained in my head. ‘Nice people,’ as she would say, ‘do not use impact as a verb. Nice people do not use passive voice. Nice people do not chew gum’—okay, so they weren’t all grammar rules.

“She was a vicious editor, and I have her to thank for making me the strong writer I am today. (But I do chew gum.)”

Moral of the story: Embrace the push to become stronger.

Jake Jacobson

Director, Public Relations, Children’s Mercy Kansas City

“I had a rhetoric professor in grad school say to me, ‘Jake, I can tell you are trying to say something, but I don’t know what it is.’ I had written a very scholarly-sounding paper using what I thought was academic language, and when I tried to write in a way that I thought would resonate with my professor, I wasn’t able to convey what I wanted, and it was frustrating for both of us. When I shifted to a more conversational tone, I was far more successful – and had more fun in the process. That experience helped me to be myself and be authentic.” 

Moral of the story: Be you and play to your strengths.

Geoff Ables

Managing Partner, C5 Insight

“This particular mentor worked with us in a leadership training program early in my career. He dumped out a puzzle and told us to put it together—taking the box cover with him. He revisited us after 5 minutes and asked what we needed. We all answered, ‘the picture’—which he then described to us. Returning 5 minutes later, he asked the same question, and this time we said, ‘Let us see the picture.’ So he briefly showed us the picture and then left again. On his final visit, he asked the same question, and we said, ‘Leave the picture with us.’ 

“He returned 5 minutes later and asked us at what point did we make the most progress. The obvious answer was ‘When we could see the picture.’ But it’s amazing how few leaders really take the time to make the picture clear to their teams. The clearer you can make the picture of your vision, the faster the progress your team will make towards that vision.”

Moral of the story: Articulate a clear picture of your vision.

Dan Ginsburg

Executive Director, Corporate and Functional Communications

“One of the best traits of professional communicators and PR people is that we all love brainstorming and share our brilliance with anyone who will listen—as well as those who won’t. 

“Early in my career, I was in a meeting with my supervisor, his supervisor, and several other senior leaders. An important communications campaign was being discussed that I knew about but wasn’t directly involved in. Just as the meeting was about to end, and after an elaborate plan was presented and agreed to by all involved, I felt compelled to offer up my NEW and better idea—which the most senior leader in the room actually loved!

“My boss smiled as we left the meeting and asked me to join him in his office for what I was sure to be a congratulatory discussion [where he would] ask for me to be more involved with the campaign. Calmly, though very firmly, he asked me whether I had thought about the work and the considerable thought that my colleagues—and my boss—had given to the plan and presentation, and whether I was aware of 3 really good reasons, which he articulated in detail, for why my idea was totally unworkable.

“Before I said a word, he simply said to me, ‘Dan, every meeting is not a brainstorm, and you’re not the only one who can have a great idea.’”

Moral of the story: Be mindful of the right time, place, and venue to offer new ideas.

Joel Schwartzberg

Senior Director of Strategic and Executive Communications, ASPCA

“One of my most memorable learning experiences came in the form of a dictate to staff from a former supervisor, the executive producer of a national public media newsmagazine from a well-known public broadcaster and television program distributor.

“Never criticize an idea or a project without, in the same moment, offering a corrective suggestion. Never identify a problem without proposing a solution or a pathway to solution.’ This way, you take ownership of the situation and assume the same reaction risk as the person you’re criticizing.”

Moral of the story: Realize that when you criticize without proposing a solution, you are complaining.

Amy Yee

Chief Digital Officer, Health Standards Organization

"One of the biggest jobs of a leader is communicating—but not communicating just once, communicating repeatedly. One great example is that you usually can’t explain ‘why’ enough times. 

“Earlier in my career, I was part of a team that had been through some difficult organizational shifts, and although we introduced changes that leadership saw as positive, the rest of the staff reacted negatively. Leadership had taken for granted that the staff would see these changes as positive, but the leaders had not repeated it enough times, in enough different ways, to ensure that everyone could see the bigger picture. 

“A great mentor of mine once said ‘After you’ve repeated something 3 or 4 times, you feel like you’ve said it many times, but you probably need to say something closer to 7 or more times—depending on the situation.’ To this day, I remember the words of my mentor, and I remind myself that I should continue to communicate the ‘why’ again and again. This notion has given me more patience and empathy when I’m tempted to just forge ahead. "

Moral of the story: Inspire people by articulating the “why” clearly and often.

Monique Visintainer

Sr. Director, Executive Communications and Speechwriter for the President, Concur

"It’s hard to pick just one, but an example that stands out came years ago early in my career as an executive communications professional. A very senior leader who I worked for had a philosophy on how to treat others that was extremely genuine and one I still remember and think about today.

“He did not believe in giving people a hard time for mistakes or being super dramatic when things didn’t go as planned. He believed people would naturally be harder on themselves than he ever would be. Because of that belief, he didn’t waste energy or ‘drama,’ as he called it, on getting upset with people.

“This went a long way with his employees, especially because his boss was known for being a lot less gracious.”

Moral of the story: Put your energy in building people up as opposed to knocking them down.

Marcie Montague

Senior Manager, Executive Communications, SAS

“A leader I work with told me a story about his journey coming into a technology company. He said to me, ‘I got hired based on my technical knowledge, but all that knowledge was irrelevant after the first few weeks.’ 

“He told me that his success was all due to his ability to learn and adapt from that point on. ‘Don’t put forth effort to keep your job. Put forth effort to outgrow your job.’”

Moral of the story: Keep learning and adapting, always.

Mark Dollins

Head of Executive & Global Employee Communications, DuPont

“Earlier in my career, I was working for a global foods and beverages company. At that point in my career, I was a strong communicator, but I wasn’t strong in financial literacy. I had a leader who taught me what I needed to know about finance so that I could be a better communicator in the world of investor relations. 

“That’s when I had the realization that the role of a leader is to develop people, and I am thankful for that.”

Moral of the story: Help the person next to you (above you and under you) to grow.

Angee Linsey

Managing Director, Linsey Careers

“This learning came from one of my first jobs. My boss would give me industry literature to read: trade magazines, journals, etc. I read them and then proceeded to return them back to him. When I did, he asked me, ‘What are you doing?’ I thanked him for the read and told him that I am returning them. He responded by saying that he didn’t give them to me to simply read and return. He wanted me to come back with my thoughts on what I read. He wanted to know how I felt it applied to what the company did. He wanted my take on where it is going in the future. He essentially wanted my critical thinking in return. 

“We are all inundated by information and we sometimes don’t think about the value of critical thinking.”

Moral of the story: Take a moment to think deeper about things you’ve learned and how they apply.

Jerry Wohletz

Speechwriter, Executive Communications Manager, American Dental Association

“I grew up on a farm in Kansas and my family sold produce at farmers’ markets. Selling produce is an art—you can have the best tomato, but that’s not why customers buy it.

“My dad—the commander-in-chief on our farm—was a skilled in many things and watching him interact with customers was a master class in communication. He said, ‘A customer may love the tomato, but they'll come back over and over for that feeling they get when they interact with you.’

“That lesson informs my work as a communications professional, and it’s those farmers’ market interactions that sparked my interest in speechwriting.”

Moral of the story: People will remember you for the way you make them feel.

Janet Arnold-Grych

Internal Communications Manager, Quarles & Brady LLP

“In a previous role, I had the privilege of working with a particular CEO. She started out in the lab and worked her way up to the top position. As CEO, she had ultimate responsibility for the strategies of the organization and working with the many internal and external clients of the firm.

“It would have been easy to get lost in the numbers, the data, the demands, and only see the ‘business side’ of the organization. But this CEO never lost her deep connection to the people we were serving: the men, women, and children who needed our help every day, every hour. When the individuals we helped or their families periodically came in to speak with us, our CEO was often visibly moved by their stories.

“She always saw real people at the end of our efforts and was committed to ensuring employees saw that, too. That type of authentic leadership served as a guide across the organization and drove our efforts. She taught me that there is nothing more powerful than a leader's true commitment to mission. From a communications standpoint, you can't fake that.”

Moral of the story: People want to rally behind something bigger than themselves.

Mary Stenander Vick

Chief of Staff & Executive Office Communications, Caterpillar Inc.

“This was at a time of a major corporate restructuring and downsizing initiative. I was new into a leadership position and the situation was very uncomfortable. A leader told me that I should ‘get comfortable being uncomfortable.’

“This lesson taught me that it is OK to not always know all the answers, to have open and frank conversations with others to search for clarity, and that being uncomfortable is when my attention to detail is best. Because of this, my skills were sharpened and I grew the most.

“I love sharing this lesson because it is easy to remember and it makes others feel better!

I feel like I use the skills learned during this time of my career every day now, even as our business is strengthening. Sometimes, it is hard to be OK with not knowing what to do or how to do it, but if you use your problem-solving skills and relationships with others, you normally can easily find your way!”

Moral of the story: Get comfortable being uncomfortable, it’s where magical things happen.

A final lesson I'd like to leave you with

The thing is, there are many lessons out there and so many ways to excel in your career. If you take anything away from this article, it should be that you are always a student and always learning. 

In my role at Local Wisdom, I still keep my former boss in mind as I actively make decisions that affect the entire company and continuously learn from everyone around me. For that, I will forever remain thankful.